Facile synthesis of terrylene and its isomer benzoindenoperylene

被引:59
作者
Avlasevich, Y [1 ]
Kohl, C [1 ]
Müllen, K [1 ]
机构
[1] Max Planck Inst Polymer Res, D-55128 Mainz, Germany
关键词
D O I
10.1039/b516264e
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
3-(1-Naphthyl) perylene was synthesised by a palladium-catalysed cross-coupling reaction of 3-bromoperylene and 1-naphthaleneboronic acid. Oxidative cyclodehydrogenation of 3-(1-naphthyl) perylene selectively afforded terrylene or its isomer, benzo[4,5] indeno[1,2,3-cd] perylene. The yield of terrylene, an important fluorophore for single molecular spectroscopy, was significantly improved in comparison to literature methods. Benzoindenoperylene has an absorption maximum at 508 nm and shows no fluorescence in contrast to terrylene.
引用
收藏
页码:1053 / 1057
页数:5
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共 32 条
[1]   Design of near-infrared dyes based on π-conjugation system extension. theoretical evaluation of arylimidazole derivatives of perylene chromophore [J].
Adachi, M ;
Nagao, Y .
CHEMISTRY OF MATERIALS, 1999, 11 (08) :2107-2114
[2]   Zeeman effect of single-molecule lines [J].
Bauer, M ;
Kador, L .
CHEMICAL PHYSICS LETTERS, 2005, 407 (4-6) :450-453
[3]  
Berlman I.B., 1971, Handbook of Fluorescence Spectra of Aromatic Molecules
[4]   Spectroscopic properties and site origin of Shpol'skii system-terrylene in n-nonane [J].
Biktchantaev, I ;
Samartsev, V ;
Sepiol, J .
JOURNAL OF LUMINESCENCE, 2002, 98 (1-4) :273-279
[5]  
BONNEN A, 1990, ANGEW CHEM, V29, P525
[6]  
BONNEN A, 1990, ANGEW CHEM, V102, P548
[7]  
BUCHTA E, 1962, LIEBIGS ANN CHEM, V660, P33
[8]   POLYCYCLISCHE VERBINDUNGEN .5. SYNTHESEN DES TERRYLENS [J].
BUCHTA, E ;
VATES, H ;
KNOPP, H .
CHEMISCHE BERICHTE-RECUEIL, 1958, 91 (01) :228-241
[9]   AROMATISCHE KOHLENWASSERSTOFFE .48. SYNTHESEN VON BENZOLOGEN DES PERYLENS UND BISANTHENS [J].
CLAR, E .
CHEMISCHE BERICHTE-RECUEIL, 1949, 82 (01) :46-60
[10]   DAS KONDENSATIONSPRINZIP, EIN EINFACHES NEUES PRINZIP IM AUFBAU DER AROMATISCHEN KOHLENWASSERSTOFFE (AROMATISCHE KOHLENWASSERSTOFFE) .42. [J].
CLAR, E .
CHEMISCHE BERICHTE-RECUEIL, 1948, 81 (01) :52-63